$71 Cheap Flights from Chicago (ORD) to Pensacola (PNS)

View $71 flight on Sat, May 10, 2025Opens in a new window
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Cheap Flights from Chicago to Pensacola (ORD-PNS)

Prices were available within the past 7 days and start at $71 for one-way flights and $142 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sun, May 4 - Sat, May 10
ORD
Chicago
PNS
Pensacola
$142 Roundtrip, found 7 hours ago
$142
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Sun, May 4 from Chicago to Pensacola, returning Sat, May 10, priced at $142 found 7 hours ago
Spirit Airlines
Fri, May 9 - Sat, May 10
ORD
Chicago
PNS
Pensacola
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, May 9 from Chicago to Pensacola, returning Sat, May 10, priced at $148 found 1 day ago
Spirit Airlines
Sun, May 4 - Wed, May 14
ORD
Chicago
PNS
Pensacola
$160 Roundtrip, found 4 hours ago
$160
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sun, May 4 from Chicago to Pensacola, returning Wed, May 14, priced at $160 found 4 hours ago
Spirit Airlines
Fri, Jun 6 - Mon, Jun 9
ORD
Chicago
PNS
Pensacola
$164 Roundtrip, just found
$164
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jun 6 from Chicago to Pensacola, returning Mon, Jun 9, priced at $164 just found
Spirit Airlines
Fri, May 9 - Sat, May 17
ORD
Chicago
PNS
Pensacola
$165 Roundtrip, found 9 hours ago
$165
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Fri, May 9 from Chicago to Pensacola, returning Sat, May 17, priced at $165 found 9 hours ago
Spirit Airlines
Mon, May 12 - Thu, May 22
ORD
Chicago
PNS
Pensacola
$167 Roundtrip, found 4 hours ago
$167
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Mon, May 12 from Chicago to Pensacola, returning Thu, May 22, priced at $167 found 4 hours ago
United
Sat, May 17 - Wed, May 21
ORD
Chicago
PNS
Pensacola
$171 Roundtrip, just found
$171
Roundtrip
just found
Select United flight, departing Sat, May 17 from Chicago to Pensacola, returning Wed, May 21, priced at $171 just found
Southwest Airlines
Wed, Jun 25 - Wed, Jul 2
ORD
Chicago
PNS
Pensacola
$187 Roundtrip, found 2 hours ago
$187
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Jun 25 from Chicago to Pensacola, returning Wed, Jul 2, priced at $187 found 2 hours ago
Delta
Tue, Jul 8 - Sun, Jul 13
ORD
Chicago
PNS
Pensacola
$190 Roundtrip, found 3 hours ago
$190
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Jul 8 from Chicago to Pensacola, returning Sun, Jul 13, priced at $190 found 3 hours ago
American Airlines
Sat, Jul 5 - Sun, Jul 13
ORD
Chicago
PNS
Pensacola
$203 Roundtrip, found 9 hours ago
$203
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Sat, Jul 5 from Chicago to Pensacola, returning Sun, Jul 13, priced at $203 found 9 hours ago

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) cost?
Cheap round-trip fares from O’Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) start at $177. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving ORD on May 12 2025 and touching down at PNS. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from ORD to PNS?
The cheapest flights from ORD to PNS are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
Fly directly from O’Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) on a United Airlines flight.
What is the cheapest airline that flies from ORD to PNS?
With fares starting at $89 for a one-way journey from ORD to PNS, American Airlines is currently the cheapest carrier flying this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on July 20 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
On average, there is just 1 nonstop flight leaving from O’Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) per day. If this doesn’t fit your plans, consider flights with layovers. Just filter your search results on Expedia to include one stop or more to discover the next best option.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
The 10 AM departures from ORD to PNS are the most sought after. Prices can be higher for these popular slots. If you want to save money, choose a less crowded time to fly.
What day of the week has the most flights from ORD to PNS?
Jet off on a Sunday if you’re after the largest selection of flights from O’Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
Take the earliest flight at around 10:53AM UTC-6, departing from O’Hare Intl. Airport (ORD). You’ll be flying for roughly 2h 30m, touching down at Pensacola Intl. Airport (PNS) at approximately 1:23PM UTC-6.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
Flights from ORD to PNS have an average travel time of 2 hours and 30 minutes. The distance between the two airports is 800 mi.
What airline has the least delays from ORD to PNS?
With 89% of flights usually arriving as scheduled, American Airlines has the best on-time performance for direct flights from O’Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS). To monitor your flight status and get notified about any changes, use the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
Opt for a flight from O’Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) that takes off before 3 PM to reduce the risk of cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Pensacola from O'Hare Intl. Airport (ORD)?
Browse your flight options from O’Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS). This is the only airport in Pensacola you can land at if you’re taking a direct flight.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) last-minute?
Last-minute bookings from ORD to PNS are generally more expensive. For the lowest prices, start looking for flights ahead of time. That said, if you’re flexible with your travel plans, it’s possible to find a cheap fare just before your departure.
Is it cheaper to book an ORD to PNS flight and hotel package?
Securing an ORD to PNS flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Pick from our extensive range of hotels and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
In most cases, you can cancel or modify your ORD to PNS flight. However, there may be additional fees, especially if you booked over 24 hours ago. Double-check your itinerary for the airline’s policies and fees on flight changes, or if you want more information, visit our Customer Service portal.
*Available to One Key members.